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2-(3-cyano-4-substituted phenyl)-4-methyl-1,3-selenazole-5-carboxylic acid and its ester compounds and preparation method

A kind of compound, the technology of allyloxy phenyl, applied in the field of medicine, can solve the problems such as unreported

Inactive Publication Date: 2016-06-15
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 2-(3-cyano-4-substituted phenyl)-4-methyl-1,3-selenazole-5-carboxylic acid and its esters have not been reported as xanthine oxidase inhibitors

Method used

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  • 2-(3-cyano-4-substituted phenyl)-4-methyl-1,3-selenazole-5-carboxylic acid and its ester compounds and preparation method
  • 2-(3-cyano-4-substituted phenyl)-4-methyl-1,3-selenazole-5-carboxylic acid and its ester compounds and preparation method
  • 2-(3-cyano-4-substituted phenyl)-4-methyl-1,3-selenazole-5-carboxylic acid and its ester compounds and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0107] Example 1: Preparation of 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid (compound 1)

[0108] (1) Addition: 0.79g selenium powder (10mmol) was mixed with 0.46g sodium borohydride (12mmol), the system was vacuumed and then filled with nitrogen for protection; under ice bath, 20mL absolute ethanol was added to prepare sodium selenium hydride solution; Add 1.2g (10mmol) of p-hydroxybenzonitrile, reflux reaction for 6h; dropwise add 6M HCl solution to make the system acidic, continue the reaction for 1h; add 100mLH 2 O, stirred in an ice bath for 0.5h, filtered, and dried to obtain the crude product of 4-hydroxyselenobenzamide with a yield of 60%. The crude product was directly used in the next reaction without purification.

[0109] (2) Cycling: 2.0g (10mmol) of 4-hydroxyselenobenzamide crude product in 5mL ethanol solution, stirring and heating to reflux, adding 1.65g (10mmol) of ethyl 2-chloroacetoacetate dropwise, and continuing to reflux for 4h...

Embodiment 2

[0114] Example 2: Preparation of 2-(3-cyano-4-ethoxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid (compound 2)

[0115] 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid ethyl ester was prepared in the same manner as in Example 1.

[0116] Alkylation: crude 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-selenazole-5-carboxylate ethyl ester 336mg (1mmol), potassium carbonate 138mg (1mmol), 5mg Potassium iodide was mixed with 2mL DMF, and 108 mg (1 mmol) of bromoethane was added dropwise under stirring at room temperature: the reaction solution was heated to 35°C, and reacted for 8 hours; after cooling, it was poured into five times the amount of water, and the solid was precipitated, filtered with suction, washed with water, and dried to obtain 2 -Crude ethyl (3-cyano-4-ethoxyphenyl)-4-methyl-1,3-selenazole-5-carboxylate, yield 83%. The crude product was directly used in the next reaction without purification.

[0117] Hydrolysis: 2-(3-cyano-4-ethoxyphenyl)-...

Embodiment 3

[0119] Example 3: Preparation of 2-(3-cyano-4-propoxyphenyl)-4-methyl-1,3-selenazole-5-carboxylic acid (compound 3)

[0120] In addition to using the corresponding alkylating agent in the alkylation step, the same method as in Example 2 was used to prepare 2-(3-cyano-4-propoxyphenyl)-4-methyl-1,3- Selenazole-5-carboxylic acid (compound 3), the total yield is 17% (based on raw material p-hydroxybenzonitrile), its structural formula, 1 H-NMR and MS data are listed in Table-1 below.

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Abstract

The invention belongs to the technical field of medicines, relates to 2-(3-cyano-4-substituted phenyl)-4-methyl-1, 3-selenazole-5-formic acid and formate compounds, pharmaceutically acceptable salts, pharmaceutically acceptable solvates which have xanthine oxidase inhibitory activity and have the general formula of I, and a preparation method thereof, and also relates to use of the compounds in preparation of drugs for treating hyperuricemia and gout diseases. The formula I is shown in the specification, R and R' independently are H; or R and R' independently are straight chain or branched chain C1-C10 alkyl, C3-C10 ene alkyl, C3-C10 alkyne alkyl, C4-C7 naphthenic alkyl, and C7-C10 aryl alkyl.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to 2-(3-cyano-4-substituted phenyl)-4-methyl-1,3-selenazole-5-carboxylic acid and its ester compounds and preparation methods, in particular to 2 -(3-cyano-4-substituted phenyl)-4-methyl-1,3-selenazole-5-carboxylic acid and its esters, pharmaceutically acceptable salts, pharmaceutically acceptable solvates and their preparation methods, and the use of these compounds in medicine. Background technique [0002] Gout is a global metabolic disease, and its prevalence is affected by various factors such as economic development, environment, eating habits, race, genetics, medical level, diagnostic criteria and statistical methods, so reports vary from country to country larger. According to available data, the prevalence of hyperuricemia in Europe and the United States is about 2% to 18%, and the prevalence of gout is 0.2% to 1.7%. In the indigenous population of the South Pacific, hype...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D293/06A61K31/41A61P19/06
CPCC07D293/06
Inventor 张为革关奇程增进沈杞容孙俊姚飞
Owner SHENYANG PHARMA UNIVERSITY
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